1,2-Dichloroethane → Methyl 2-[(4-{2-[benzyl(hexyl)amino]-2-oxoethyl}phenoxy)methyl]benzoate

HRID 899872

Reaction equation

HRID 899872 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:22]=[CH:21][CH:20]=[CH:19][C:6]=1[CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][C:16]([OH:18])=O)=[CH:11][CH:10]=1)=[O:4].[CH2:23]([NH:29][CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[CH2:24][CH2:25][CH2:26][CH2:27][CH3:28].C(Cl)CCl.Cl>C(Cl)Cl.CN(C1C=CN=CC=1)C.O>[CH2:30]([N:29]([CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[C:16](=[O:18])[CH2:15][C:12]1[CH:11]=[CH:10][C:9]([O:8][CH2:7][C:6]2[CH:19]=[CH:20][CH:21]=[CH:22][C:5]=2[C:3]([O:2][CH3:1])=[O:4])=[CH:14][CH:13]=1)[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Participants

8

Reactant 4

HCID 111,2-DichloroethaneHCID 313Hydrochloric AcidHCID 485395Benzenemethanamine, N-hexyl-HCID 68869545[(4-{[2-(Methoxycarbonyl)benzyl]oxy}phenyl)]acetic acid

Product 1

HCID 69120595Methyl 2-[(4-{2-[benzyl(hexyl)amino]-2-oxoethyl}phenoxy)methyl]benzoate

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

(4-{[2-(Methoxycarbonyl)benzyl]oxy}phenyl)acetic acid (50 mg, 0.166 mmol) was dissolved in DCM (2 ml), N-hexylbenzylamine (38.2 mg, 0.2 mmol) was added, then EDC (38.3 mg, 0.2 mmol) was added and then DMAP (24.4 mg, 0.2 mmol) was added. The mixture was stirred at room temperature overnight. 1% HCl (1 ml) and water (1 ml) were added into the mixture. The two phases were separated by using a Whatman Filter Tube. The obtained organic solution was evaporated in vacuum and the oil product (71 mg) was left. It was then used directly in next step.

Workup

  1. customThe two phases were separated
  2. filtrationFilter Tube
  3. customThe obtained organic solution was evaporated in vacuum
  4. waitthe oil product (71 mg) was left

Sources & evidence

ORD record
ord-1872da0ec55046f98d92796f95ad8e2e
Source dataset
uspto-grants-2008_04
Patent number
US07355069B2

Linked notes

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